Makawao/Olinda/Haliimaile Homes for Sale

Welcome to the enchanting neighborhoods of Makawao, Olinda, and Haliimaile, nestled in the lush, green hills of Maui, Hawaii. Renowned for their rich history and vibrant culture, these charming communities offer a unique blend of island living and rural tranquility.

Makawao, often referred to as the "Paniolo (cowboy) Town," is steeped in Hawaiian ranching history, boasting a plethora of art galleries, boutiques, and local eateries that celebrate the spirit of the island. Stroll down Baldwin Avenue and immerse yourself in the warm, welcoming atmosphere, where the community gathers for events and festivals throughout the year.

Just a short drive away, Olinda captivates with its breathtaking views and cooler climate, making it a favorite spot for those seeking a serene retreat. The neighborhood is dotted with beautiful homes, many of which feature expansive gardens and stunning vistas of the Pacific Ocean and neighboring islands.

Haliimaile, a quaint community with a rich agricultural heritage, offers a peaceful escape while still being close to the amenities of Makawao. The area is known for its lush landscapes and friendly neighbors, making it an ideal place for families and nature lovers alike.

For those considering a move to this idyllic region, there are a variety of homes for sale that cater to different tastes and budgets. Whether you’re looking for a cozy cottage or a sprawling estate, the real estate options in Makawao, Olinda, and Haliimaile are as diverse as the landscape itself. Embrace the Hawaiian lifestyle and discover your dream home in these beautiful neighborhoods today!

Newest Makawao/Olinda/Haliimaile Homes for Sale

156 Alaluana Rd, Makawao $1,650,000

Follow the country road to the very top of Piiholo Road, where peaceful Upcountry living, privacy, and breathtaking surroundings await. Nestled on this exceptional 3 Acre...

ACTIVE Status
2 Beds
2 Baths
410267 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(P)

Listing courtesy of Coldwell Banker Island Prop(P).

37 Pukiki Pl Unit B, Makawao $999,000

Nestled on a private road, 37 Pukiki Place offers the peace, privacy, and tranquility that define Upcountry Maui living. This recently renovated single-level residence is...

ACTIVE Status
2 Beds
1 Baths
410243 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

35 Pukiki Pl Unit A, Makawao $1,499,000

Tucked away on a peaceful private road, 35 Pukiki Place presents a rare opportunity to enjoy the best of Upcountry Maui living in one of the island’s most desirable micro...

ACTIVE Status
6 Beds
4 Baths
410242 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

94 Leiohu Cir, Makawao $2,288,888

Be the first to call this brand-new home, completed in 2026, your own! Located in the very sought out Kualono subdivision, this thoughtfully designed 3-bedroom, 3.5-bath ...

ACTIVE Status
3 Beds
4 Baths
410231 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

1740 Piiholo Rd, Makawao $2,649,000

Crest the rolling hills and you’ll discover this breathtaking Upcountry Maui estate: a one-of-a-kind property with a rare combination of privacy, expansive space, and tim...

ACTIVE Status
5 Beds
4 Baths
410159 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

1131 Kehau Pl, Makawao $1,098,000

Perched just above Makawao Town, 1131 Kehau Place captures the essence of Upcountry living with sweeping ocean and West Maui Mountain views, cool trade winds, and the con...

ACTIVE Status
3 Beds
2 Baths
410138 MLS
Fee Simple Tenure

Courtesy of Compass-W

Listing courtesy of Compass-W.

15 Olinda Rd, Makawao $2,395,000

Also listed under Multi-Dwelling (MLS 409725). This unique multi-unit property (4 structures, 8 units) offers a rare opportunity for investors seeking strong cash flow an...

ACTIVE Status
5 Beds
4 Baths
409724 MLS
Fee Simple Tenure

Courtesy of eXp Realty

Listing courtesy of eXp Realty.

2840 Koea Pl, Makawao $989,000 ▼

Perched in coveted Upcountry Maui, this original Plantation-style 3-bedroom home captures breathtaking north and south shore views, sweeping across the entire Central Val...

ACTIVE Status
3 Beds
2 Baths
409804 MLS
Fee Simple Tenure

Courtesy of Corcoran Pacific Properties

Listing courtesy of Corcoran Pacific Properties.

1088 Mamalu Pl, Makawao $968,000 ▼

Incredible Value in Makawao! Discover the charm of Upcountry living in this maintained single-level home, ideally situated on a quiet cul-de-sac in one of Makawao's most ...

ACTIVE Status
3 Beds
2 Baths
409182 MLS
Fee Simple Tenure

Courtesy of Compass

Listing courtesy of Compass.

3586 Kalua Pl, Makawao $1,150,000 ▲

Your whole family will have space in this energy efficient, turnkey, Bungalow Style, multi-level "Mini Mansion" It's nestled Upcountry on Haleakala. Walking distance to ...

ACTIVE Status
3 Beds
2 Baths
408939 MLS
Fee Simple Tenure

Courtesy of Nathalie Mullinix Rlty Universal Inc

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

2400 Piiholo Rd, Makawao $1,399,000 ▼

Bring your vision to this peaceful Upcountry property nestled just below the cool cloud line of Upper Piiholo. Set on two (2) beautifully established acres, this three (...

ACTIVE Status
3 Beds
2 Baths
408348 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(Ka)

Listing courtesy of Coldwell Banker Island Prop(Ka).

1199 Freitas Pl, Makawao $1,495,000 ▼

Welcome to 1199 Freitas Place in Makawao town — a well-cared-for home that combines functional design with classic island living. This is truly one of the best values in ...

ACTIVE Status
3 Beds
2 Baths
407661 MLS
Fee Simple Tenure